1-(2-Hydroxyethyl)-1H-benzimidazole-7-carbonitrile → (7-Cyano-1H-benzimidazol-1-yl)acetic acid

HRID 1991204Notes

Reaction equation

HRID 1991204 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[C:9]([C:13]#[N:14])=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1.BrC1C2N(CC(O)=[O:27])C=NC=2C=CC=1>>[C:13]([C:9]1[C:8]2[N:4]([CH2:3][C:2]([OH:27])=[O:1])[CH:5]=[N:6][C:7]=2[CH:12]=[CH:11][CH:10]=1)#[N:14]

Participants

3

Reactant 2

HCID 114467811-(2-Hydroxyethyl)-1H-benzimidazole-7-carbonitrileHCID 11470826(7-bromo-1H-benzimidazol-1-yl)acetic acid

Product 1

HCID 11195002(7-Cyano-1H-benzimidazol-1-yl)acetic acid

Procedure

(7-Cyano-1H-benzimidazol-1-yl)acetic acid was prepared starting from 1-(2-hydroxyethyl)-1H-benzimidazole-7-carbonitrile (89 mg) according to the procedure described for the synthesis of (7-bromo-1H-benzoimidazol-1-yl)acetic acid. Yield 38 mg (39 %). MS (ESI) m/z 202.0 [M+H). 1H NMR (400 MHz, DMSO-D6) δ ppm: 5.31 (s, 2 H), 7.37 (dd, J=8.1, 7.7 Hz, 1H), 7.75 (dd, J=7.6, 0.8 Hz, 1H), 8.04 (dd, J=8.1, 1.1 Hz, 1H), 8.38 (s, 1H), 13.43 (bs, 1H).

Sources & evidence

ORD record
ord-4cd6631c79394a3bbf569b593e90bad4
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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